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17.5 The Wittig and Related Reactions PowerPoint PPT Presentation

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Main Menu. 17.5 The Wittig and Related Reactions. The Wittig Reaction (formation of alkenes). General Reaction:. R´ and R” can be H or alkyl group. Phosphine oxide. Wittig reagent (a phosphonium ylide ). General Reaction:. base. Formation of Wittig Reagents. A phosphonium salt.

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17.5 The Wittig and Related Reactions

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17.5 The Wittig and Related Reactions

The Wittig Reaction

(formation of alkenes)

General Reaction:

R´ and R” can be H or alkyl group.

Phosphine oxide

Wittig reagent (a phosphoniumylide)

General Reaction:


Formation of Wittig Reagents

A phosphonium salt

Ph: phenyl

  • The alkyl halides need to have at least one H.


Potassium tert-butoxide

Mechanism of Wittig Reaction



Examples of Wittig Reaction



Wittig reagents favor the Z (cis) isomer.

Horner-Emmons reaction (general reaction):

Reactions of Aldehydes and Ketones with Horner-Emmons Reagent

R = Et (most common)

Phosphate diester

Horner-Emmons reagent

Arbuzov (Perkow) reaction:

Formation of Horner-Emmons Reagent


Stabilized carboanion

R = alkyl, acyl or R’OC(O)-

Mechanism of Horner-Emmons Reaction



Water insoluble

Water soluble

Examples of Horner-Emmons Reaction

> 99%

Horner-Emmons reagents favor the E (trans) isomer.

1. What could be the reagent for the following transformation?

Learning Check

2. What should be the product from the following reaction?

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3. What could be the product for the following reaction?

Learning Check

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